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Michael in Drag

Summary:

“Would you really do that?”

Mike starts to worry when he notices that Will never talks about girls or seems interested in having a girlfriend. Thinking he’s only being helpful, Mike pretends to be a girl so Will can practice.

Notes:

hi. clarifications: english is not my first language n this is my first time publishing fanfiction. ;)

plus. mike it's STUPID n the word girlfriend is going to haunt me. srs.

It will have a total of 7 chapters, maybe if I think of more things I can write more!!

Chapter 1: Girlfriend.

Chapter Text

Mike hadn’t planned to think about it so much. The thought had just stayed in his head once it crossed his mind.

It wasn’t the first time he’d thought about it. During the past summer, it had been impossible not to notice that everyone in the group had found someone. Lucas and Max. Dustin and Suzie. El and him. Even his sister had been all clingy with Jonathan.

Everyone had someone. Everyone except Will.

At first, he hadn’t paid much attention to it. Will had always been different. Quieter. More reserved. More… himself. But over time, the idea started to stick in his head more than he’d like to admit.

How was it possible that Will had never mentioned a girl? He hadn’t seemed interested in Jennifer Hayes either when they told him she had cried at his funeral—although, to be fair, he had bigger things to worry about back then. He hadn’t shown any interest in Max when she first arrived in Hawkins either, which, at the time, Mike had been grateful for.

The only thing Mike knew about any possible romantic interest was from El’s letter, the one she’d sent from California, where she mentioned that Will had been painting a lot, maybe for a girl. But some things about that never quite added up… and besides, a lot of time had passed, and as far as Mike knew, Will hadn’t sent any letters to California. Much less called anyone.

God, had Will even kissed a girl?

I hope not, Mike wished deep down.

But the point was, Will had never talked about any of that with him. And now, after everything that had happened in California, the atmosphere between them was tense. Unbearable. The chances of talking about girls with Will right now were practically nonexistent.

Since they had returned to Hawkins, they barely spoke to each other. Now that the Byers were living in his house, where they were forced to see each other every day, that distance felt even more obvious. They ran into each other in the kitchen, in the living room, in the hallway, at any moment… and yet, it always felt like there was something invisible between them.

They only talked about stupid things. Necessary things. Quick questions. Short answers. Nothing that lasted more than a few seconds. Nothing that felt like the conversations they used to have.

Mike noticed it in every little moment.

“Are you using the TV?”
“No… I’m done.”
“Oh. Thanks.”

“Mom said dinner’s ready.”
“I’m coming.”

“Good night, Will.”
“Night.”

God, why did Mike think the best way to start talking to Will again would be by bringing up girls? He should apologize. Again.

Mike sighed, running a hand through his hair in frustration as he got off his bed and grabbed the closest clothes he could find.

He had spent the whole morning locked in his room, staring at the ceiling, going over the same stupid thought again and again. Thinking about Will. Thinking about things that shouldn’t matter to him. Thinking, especially, about why his best friend had never been with a girl.

It wasn’t his business. Not at all. He had more important things to do. Like living. Or at least pretending to be a functional person.

He had to stop thinking. He had to do something productive.

Brush his teeth. Eat breakfast. Maybe even try to have a normal conversation with the boy he’d known for more than ten years—and, of course, fail.

The first thing he saw when he went downstairs was the daily chaos of two completely opposite families living together.

Karen and Joyce had taken over the entire kitchen.

Joyce was stirring a pan with way too much energy, talking quickly about something from the grocery store, while Karen tried to keep up, checking a recipe with a focused expression… it didn’t seem to be working.

Something was burning. A dark cloud of smoke floated near the ceiling.

“Jonathan, open the window!” Joyce shouted, without stopping her cooking.

Nancy was at the table, arranging the plates at an exaggerated speed that was completely her. Her movements were fast, precise, almost robotic. She went back and forth between the table and the kitchen without stopping for a second, dodging Joyce, Karen, and the smoke as if she were already used to mornings like this.

On one of those trips, her gaze met Mike’s. Nancy frowned slightly, as if she had just locked onto him, then walked straight toward him without giving him time to react. On the way, she grabbed a box and, without warning, dropped it into his arms.

“Here,” she said, not slowing down. “Tell Holly to come eat, and leave the box in the basement.”

Before Mike could say anything, Nancy was already on the other side of the kitchen, grabbing glasses to keep setting the table. Mike blinked. “Where’s Holly?”

Nancy answered without looking at him, placing the glasses on the table. “Downstairs. In the basement.”

Mike nodded silently, even though no one was watching, and started walking carefully toward the door that led to the stairs. The box was heavier than he’d expected—or maybe it just felt heavy because he had no idea what was inside. It sounded like it was full of loose things, shifting every time he took a step, forcing him to move more carefully than necessary.

When he reached the basement door, he adjusted the box against his chest, turned slightly, and pushed the door open with his shoulder. It creaked softly as it opened. He slipped inside sideways, almost losing his balance, and made it through just before the door closed on its own.

He started going down the stairs slowly, careful not to trip, feeling the wood creak beneath his sneakers. The basement was quieter than the rest of the house, with soft light coming in through a small window and a silence that completely contrasted with the noise upstairs.

Holly was sitting on the floor, sheets of paper and colored pencils scattered around her. Her tongue stuck out slightly as she focused on her drawing. Beside her, Will was leaning toward her, pointing at something on the page with patience, quietly explaining what she could improve.

Mike froze for a second.

He hadn’t expected to find Will there. Or rather—he hadn’t even thought about it. Of course he’d be there. He’d been sleeping in the basement for months.

“Hi…” he said finally, the word coming out too soft, almost unsure of itself. Nerves rushed through his body the moment he spoke.

Will looked up instantly.

His hair was still wet, a little messy, like he’d showered recently and hadn’t bothered to comb it. He didn’t look bad. Will never looked bad. A few drops were still sliding down his neck, disappearing beneath the collar of his shirt. Their eyes met for a moment that felt endless, and it was enough for Mike to completely forget how to talk.

Holly looked at him too, grinning widely.
“Hi, Mike!” Her voice was full of excitement. “Will is helping me with my homework. We have to draw.”

She proudly showed him the page, covered in crooked lines and mixed colors. Will looked away almost immediately, lowering his gaze back to the paper, as if concentrating was the only thing he could do right now. “Morning,” he murmured.

Mike swallowed. He had officially lost whatever few social skills he had left.

“G-good morning,” he replied, setting the box down in a corner. “Uh… breakfast’s almost ready.”

Holly packed up her pencils and papers right away, shoving them into her pencil case without much order. She snapped it shut, stood up, and looked at Will with a grateful smile.

“Thanks for helping me,” she said, and before he could react, she wrapped her arms around him in a quick, tight hug.

Will froze for a second before awkwardly returning it with a small pat on her back. Holly grabbed her things, rushed past Mike, and ran up the stairs. Within seconds, her footsteps were gone, leaving the basement in a strange, oversized silence.

And there Mike was, once again, stuck in a situation that painfully reminded him that things with Will weren’t the same anymore.

What torture. It wasn’t that he minded being with Will. He never had. It had always been the opposite. Being with him had always been the easiest thing in the world.

But now it was different. Guilt flooded his chest every time they stood like this, facing each other with nothing to say. Every time the silence stretched too long. Every time he desperately searched for something to talk about and found nothing.

Because it hadn’t been like this before.

Before, they could spend hours alone without running out of words. They talked about everything. Games. Movies. Stupid dreams. Weird theories. Important things. Useless things. Time passed without them even noticing.

Mike lowered his gaze slightly, tightening his grip on the box, trying to ignore the knot in his throat.

Will was the first to move. He slowly stood up, brushing his hands together, as if gathering the courage to say something.

“Let’s go,” he murmured at last.

His voice sounded calm. Normal. Like nothing was wrong. Like there wasn’t an invisible wall between them. Mike looked up and nodded, unable to say a single word. He just followed him.

They went up the stairs in silence, one behind the other, not touching, not looking at each other too much, their footsteps mixing with the voices coming from the kitchen. With every step, Mike felt his chest tighten a little more.

When they reached the top, the chaos had simply changed form.

Now everyone was sitting around the table.

Mike walked in behind Will, looking for a place to sit without really knowing where, feeling out of place even in his own house.

Breakfast went on like always. Loose comments. The sound of cutlery. Glasses touching the table. Overlapping conversations. Karen and Joyce talked about the grocery list. Nancy argued with Jonathan about something she’d seen on TV. Ted ate in silence.

After eating, Karen and Joyce were the first to stand up, getting ready to go shopping and drop Holly off at school. Will and Mike didn’t have classes that morning. Schedules during quarantine had been a mess lately. They changed all the time. Got canceled without warning. Overlapped. Neither of them complained. Skipping class didn’t sound that bad.

Will stood up and started gathering the plates one by one, moving calmly. Mike watched him without realizing it, following the way he walked back and forth, how he balanced everything in his arms before heading to the kitchen.

He watched him disappear through the doorway.

Ted had already claimed the couch and the TV. In the corner of the table, Nancy and Jonathan were sitting way too close. Their shoulders touched. They spoke quietly. Smiled at everything. Nancy rested her hand on his arm every two seconds.

Too close. Too together. Too… groos.

Mike rolled his eyes and, before he could hear any comment he didn’t want to hear, stood up, grabbed his plate, and went to the kitchen. When he walked in, the first thing he saw was Will’s back at the sink.

His sleeves were rolled up, hands under the running water, focused on scrubbing a plate with the sponge. Sunlight came in through the window, hitting his hair and making it look lighter.

Mike froze for a second. An opportunity. Take it.

He took a deep breath, walked over, grabbed a sponge, and started washing his own plate. Pretending to be natural, even though the slightest brush of his shoulder against Will’s made his skin prickle.

“They have no shame,” he blurted out, forcing his voice to sound casual. Forcing himself not to sound as nervous as he felt.

Will flinched slightly, like he hadn’t noticed Mike was there.

“What?” he asked, turning his head a little.

“Nancy and Jonathan,” Mike said quickly. “Jeez. I had to escape before becoming the third wheel.”

He tried to sound relaxed. Normal. Like he wasn’t measuring every word. When Will let out a small laugh, Mike finally relaxed a little.

He placed a plate on the rack and grabbed another. “Yeah,” Will said softly. “I know how that feels.”

And the words hit Mike straight in the chest. Because he knew exactly what he meant. It was his fault. In California, so focused on El that he’d forgotten about his best friend. In the summer, too busy with girlfriends to make time for Will.

Memories crashed into him all at once, along with a familiar wave of guilt. He squeezed the sponge slightly and swallowed. Maybe it was time to talk about that.

“It doesn’t have to be like that, y’know?” he said.

Will made a small confused sound. Mike cleared his throat and went on. “I mean—you’re amazing, Will. You could get a girlfriend, and then I’d be the third wheel. It’d be my karma.”

Will lowered his gaze to the soapy water, as if it had suddenly become the most interesting thing in the world. He moved the plate slowly, not really cleaning it, just letting it turn in his hands.

“I guess… sometimes you get interested in someone different from you,” he said quietly.

His tone was so casual it sounded rehearsed. “Like… someone who has nothing to do with you. Different. In every way.”

Mike frowned slightly, feeling the words echo in his head longer than they should. Different how? In what way? He wanted to ask, but didn’t dare.

“Different…?” he repeated softly.

Will let out a short, nervous laugh and shook his head. “Forget it. It doesn’t matter.”

He stayed quiet for a few seconds, then sighed. “The truth is… I don’t know how to do this stuff, Mike. I don’t know how to go out with a girl. What to say. When to talk. When to shut up.”

He placed the plate on the rack harder than necessary. Something tightened in Mike’s chest. He knew that tone.

He’d heard it a thousand times when they were younger. When Will said he didn’t understand people. That he was always one step behind.

And without thinking, he spoke. “It’s not complicated.”

Will looked up. “It’s not?”

Mike hesitated for a second, but he was already in too deep.
“If you want, I can… I don’t know. Help you. Practice or something.” He smiled a little. “We could… spend time together again.”

Will stared at him, a strange mix of confusion and something else Mike couldn’t quite read in his eyes.

“Would you really do that?”

Mike felt his heart beating way too fast for something that was, in theory, a normal proposal—helping his friend get a girlfriend, teaching him what to do, and finally getting rid of those thoughts about Will being single that haunted him. “Yeah. Of course,” he replied quickly. “We’re… we’re us, right?”

“I don’t think it’s necessary. I’m not interested in… girlfriends.” Will murmured, his voice unsure, fading with every word. Mike watched him, trying to come up with an excuse, something—he needed to get Will a girlfriend, for… for… that’s what friends did! So Will wouldn’t be alone, and so Mike— shut up

“It’ll help you in the future. That pretty face of yours is going to drive girls crazy, Will, I promise.”

Will sighed, washing the last plate and drying his hands with a towel. Then he tilted his head slightly and looked at Mike with a hint of mischief. “Oh, are you an expert, Mike? Because El du—”

Mike cut him off before he could finish the word. “No, no, no, I’m not. I guess I know… the basics. Besides, I don’t think you’d make the same mistakes I made with El. You’re not an idiot.”

“Yeah. And my name isn’t Michael Wheeler.”

“Yeah, and your name isn’t Michael Wheeler,” Mike murmured with a smile as he spread his hands to dry them, droplets lightly spotting his clothes. He looked back at Will, not knowing exactly what to do or say. “Um… so?”

Will rolled his eyes with a small smile—at least that made it clear Mike hadn’t made him uncomfortable, because Mike would’ve wanted to end his own life right there. He’d failed too many times trying to talk to Will over the past few months. “I think it’s stupid.”

Will’s words were direct. Yeah, he was right. It was stupid. Every idea Mike had was stupid. He should’ve just kept quiet. Why would Will need help from Mike anyway? After all, Will knew how stupid he’d been with his sister. He probably knew Mike could barely even say “I love you.” Maybe it was a lie that Will didn’t know how to deal with girls. Maybe he just didn’t want to, and maybe he was actually great at flirting—so good he wouldn’t even need to listen to anything Mike had to say. Probably, if Will followed Mike’s advice, all his future relationships would fail. And that would mean Will Byers staying single. And that would mean Mike would have to deal with—no.

“It is,” Mike whispered. If his thoughts hadn’t reminded him of that, he probably would’ve kept trying to convince Will, searching for more believable excuses to help him get a girlfriend.

“But I guess it wouldn’t be so bad to spend time with you again.”

Will’s words were so sudden and unexpected that Mike had to process them. Will wanted to spend time with him? Wow. Wow. That was hard to believe.

Mike’s eyes lit up. Maybe things between him and Will weren’t as bad as he’d thought. Maybe all the awkward conversations he’d created had just convinced him that everything was ruined, that they’d never be best friends again, that once all this was over—once they beat Vecna and saved the world, once the Byers found a place to live, once they finished college and went their separate ways—Will would stop talking to him.

The idea had haunted him for a long time. He didn’t want that. He didn’t want to lose Will. He couldn’t lose him. And he’d tried so hard to make things go back to how they were, only for Will to now say he wanted to spend time with him—even if that meant listening to his stupid advice that he probably wouldn’t even use, because Will surely knew how to do everything way better than Mike.

“Yeah?”

Will’s lips curved into a small smile. He held eye contact for a few seconds before looking away and rubbing the back of his neck. “…I guess.”

Mike stayed quiet for a moment, watching him, like he still couldn’t believe Will had really said that. That he wanted to spend time with him. With him. Not because he needed help. Not because he was confused. Not because Mike insisted. Just because… he wanted to.

“So…” he murmured, almost unsure. “Do you wanna go to my room?”

As soon as the words left his mouth, he regretted them. They sounded weird. Too direct. Too obvious. Like he was expecting something else. He noticed Will looking down, playing with the sleeve of his hoodie, rocking slightly on his feet. Overthinking, as always. Did it sound suggestive? No. No—

“Sure.”

And without saying anything else, they both started leaving the kitchen with slow steps, heading toward the stairs in complete silence. Why did it feel so tense? Mike didn’t know, but he was determined. He was going to help his best friend, Will Byers, get a girlfriend.

Mike jumped when he felt a sudden tug on his arm just two steps up. He turned and saw his sister. “Mike.”

“What?” he muttered in his usual uninterested tone.

“The school called. They’re letting students out early because of some issues.”

No. Not now. Not when things were finally going right. God, it felt like fate always found a way to ruin everything.

“I have—”

“We can do it later,” Will murmured behind him, and Mike turned instantly, raising an eyebrow. Fate was definitely against him. No doubt about it. “I’ve got some things to do.”

Mike took a few seconds and sighed, nodding slightly. “Okay.”

He went back down the two miraculous steps and shot Nancy an annoyed look. She had already turned back to Jonathan. Wow. Great. Just great.

He left his house way too fast, pulling out his bike and starting his ride.

Thinking about it, it wasn’t that bad. Honestly, he didn’t even have a clear idea of what he was going to tell Will. After all, he had only dated El, and that relationship definitely hadn’t been very mature. Last summer, all they did was hang out and kiss. And during the months they were apart, Mike hadn’t even been able to write that he loved her. He hadn’t been the best boyfriend, but he was grateful that he and El had managed to end things on good terms. They’d agreed that everything was easier as friends. And it really was.

But then… what was he supposed to tell Will?

His relationship with El had mostly started because of luck. There hadn’t been flirting, hints, or anything like that. It had just happened, because El was the only girl who hadn’t been disgusted by him. Lucas had once thrown that in his face. And he’d been right. Mike should’ve listened. It would’ve saved him from hurting a girl as wonderful as El.

He’d been lucky to have her as his girlfriend. But he was even luckier that, after everything, El still wanted to be his friend. And Mike appreciated that more than he could say.

Well, maybe he could explain to Will how to talk. What to say. What to hint at. How to drop subtle signals. Lucas had told him about the things he’d done to win Max over. Maybe that would help.

Or maybe he’d just say something stupid. Will probably— jeez, Mike, stop assuming things.

Will had probably never kissed a girl. Probably hadn’t even talked to one. Or touched one. Or maybe he had, and he’d messed it up, because he didn’t know how, and now he needed Mike’s incredible help. Mike, a nerd who had ruined his relationship because he couldn’t say “I love you.” A nerd who would probably die single and virgin.

How funny that Will would need his help.

Mike sighed in frustration, running a hand through his hair before finally getting on his bike. He had to stop overthinking. At this point, Holly was going to be the last kid picked up from school.

The air hit his face as he started pedaling. The dark strands on his forehead flew in every direction, some blocking his view. Annoying. He should cut his hair. It was even longer than when he’d come back from California. He remembered his father’s disapproval when he’d let it grow. "Maybe you want a dress too, Michelle."

Gross. The memory made his skin crawl. What would his dad think now that it was even longer? Would he kick him out? It had always been too obvious that Ted didn’t want “faggots” in his house. But Mike wasn’t one. Of course he wasn’t. He just liked how he looked with long hair.

He even thought Ted should be grateful he hadn’t gone for that orange mohawk. Though he hadn’t completely ruled it out.

Mike stopped at a corner to tuck his hair behind his ears. God, he really needed a haircut. As his fingers fixed the strands that would just fall back into his face once he started pedaling again, an idea crossed his mind.

Michelle. Mike could be Michelle. For Will.

He could pretend to be a girl. Act out situations with Will so he could practice. And once Will managed to talk to him—no, to Michelle—he’d be ready to do it with a real girl. God, he was a genius.

He didn’t need to give advice he didn’t even understand. He just had to act. Maybe that would give Will the confidence he lacked when it came to girls. It wasn’t hard. He’d grown up with three women in his house. He knew Max and El. He knew how they acted. It wasn’t complicated. He was going to pull this off.

He’d cut his hair later. For now, he’d keep it as long as possible. Not even his dad’s words would make him cut it. He needed to help Will. He needed Will to get a girlfriend. He wasn’t going to stop until he did.

He started pedaling again, faster this time. And it definitely wasn’t because he was worried about being late—he’d been late a million times. Worst brother ever.

It was because he was excited. Excited to be useful. To help his friend after messing up so many times. And, of course, to spend time with Will again.

When he arrived, Holly was waiting with her bike, standing next to a teacher and other kids whose parents hadn’t arrived yet. He did what he always did: talked to the teacher, signed a paper, and started riding back home. Back to his plan.

Still, he couldn’t go too fast. Holly kept yelling at him to slow down, and he reluctantly did.

Now they were riding side by side at a calmer pace. The wind wasn’t messing up his hair as much, thankfully. Maybe fate had finally decided it was time for things to go right for Mike.

“I passed,” Holly said softly. Mike made a confused sound. He’d been lost in his thoughts. Holly frowned, annoyed that she had to repeat herself.

“The drawing I did with Will. It’s really good. He’s really good at drawing.”

“Oh. Yeah, he’s great,” Mike nodded with a smile. He liked knowing that others saw Will the same way he did. He liked that people noticed him. Will deserved it. “He’s good at everything.”

“Not really,” Holly murmured, focusing on her grip on the handlebars. “Today he told me he’s bad at saying things.”

Mike frowned, processing that. Will was good at talking. In California, he’d had so many heart-to-heart conversations with Mike. He always seemed to know exactly what to say. Why would he think that?

“That doesn’t make sense.”

For a few seconds, only the wind and the sound of their wheels filled the space between them.

“He said he never says what he feels in the moment,” Holly added with a small shrug. “And then it’s too late.”

Okay. That made more sense. Maybe Will was too scared to say what he wanted to girls. Mike—well, Michelle—could help him with that. With confidence. With words. That was it.

He inhaled and exhaled. Riding a bike tired him out way more than it used to. “I can help him with that.”

Holly just nodded, not really paying attention. She was just a kid. She probably didn’t understand the weight of Will’s words. Still, Mike was grateful she’d told him. Now he knew better how to help.

They were one block from home when Holly started pedaling faster, trying to get there first. For once, Mike let himself compete. He sped up, laughing when he beat her.

Today, everything felt like it was going right. How surprising, Wheeler.

When they went inside, they were greeted by the warm air of the house. They closed the door quickly to keep the cold out. Holly pulled a sheet of paper from her backpack and ran to the basement, yelling Will’s name. She was so excited to show him her grade.

She was lucky. She got to spend time with Will without excuses. With normal conversations. Mike just hoped he could have that too, soon.

He wiped his shoes on the mat and went to his room. The cold had exhausted him. He’d take a hot shower, then hide under his blankets until his hair dried. Then he’d make coffee and start his plan. Perfect. Everything was under control.

Will was so lucky to have him as a friend.

Mike showered quickly. He hated the cold feeling of his bare skin under the water, even if it was warm. As soon as he was done, he dried off and put on the warmest clothes he could find.

When he left the bathroom to go back to his room, something in Nancy’s bedroom caught his attention.

Oh.

Oh god.

Michelle was going to be very real. Too real.

Will had no idea what was coming. And he definitely didn’t know how fast he was about to get a girlfriend.